Making The Move To A Non-Legal Career With Nhu-Y Le [TFLP 111]

On the latest episode of the Former Lawyer Podcast, I spoke with Nhu-Y Le, Vice President of Client Services at Legalpad. Legalpad is a business immigration company that helps startups immigrate their founders and other talent to the United States about her move to a non-legal career.

Before her present non-legal career, she was laser-focused on becoming a practicing lawyer. Throughout her career, she has worked in Biglaw, in-house law, immigration law, and now, in legal tech. One of the things I love most about Y’s story is that she shares how she incrementally moved to a point where she ended up in legal tech doing a non-legal role. 

I think Y’s story is really helpful in the sense that she illustrates how you can make small moves over time and still end up in a place that works for you. Keep reading to hear more about Y’s story and to hear some advice if you’re starting to feel unsure that the law is the right path for you.

Early Ambitions

From the time that Y was a little girl, she was set on having a legal career. At eight years old, she immigrated to the US from Vietnam. She said to herself, “No matter what, I’m going to be a lawyer.” Even with a language barrier, she dedicated herself to her goals, becoming a class representative and getting on the student council during her high school years. While she didn’t have anyone in her family that was a lawyer, she knew that was her path.

Gripped by that dream and her dedication, she entered law school. However, she quickly learned that it wasn’t the right kind of environment for her. For Y, law school wasn’t the experience she felt she needed to become a lawyer. It was too long and lacked the hands-on experience that Y needed.

As most lawyers know, going to law school and practicing law are two very different things. To Y, law school was a complete waste of time. She did well in undergrad, but she did not thrive in a law school environment.

Life In Law School

Law school was the first time in Y’s life where she questioned herself and her abilities. She needed a practical approach, not a theoretical one. However, this never deterred her from her goal of becoming a lawyer.

During her second year at Boston College Law, she worked at a law firm in exchange for course credits. She was placed at Fragomen, the top business immigration law firm in the world. She worked full-time for a semester and stayed part-time until she graduated.

She left law school with a degree and a year and a half of experience working in business immigration, which set her up to continue working in that field. She really enjoyed this position, as an immigrant herself, and truly loved working for a firm that helps high-talent people come to the US was just the perfect position for Y.

Working In Immigration Law

In immigration law, lawyers get to craft that whole argument as to why someone is at the top of their field in whatever it is they want to do. It was a chance for Y to still use her writing abilities and help train paralegals to make those types of arguments for these clients.

Unfortunately, after Y graduated from law school, there were no paid positions available at Fragomen, so they weren’t able to keep her on. But one of the managing partners took Y aside and got her an interview at a boutique law firm in Washington DC the very next day.

She remained there until after she had passed her bar exam. Then, Y was offered a position at Fragomen, which she jumped at immediately. She was there for another 2 years, working with a high-profile client. 

Realizing Biglaw Was Too Much

Constantly under pressure, Y decided that this life and career path was just not what she wanted anymore. She still wanted to be in law, but she wanted something more sustainable. Eventually, a LinkedIn recruiter approached Y with an in-house position.

Thinking that in-house would be a better fit, she went in-house. There, the legal department was essentially a law firm with a thousand people in the legal department. When looking back, Y said she wished she took more time to think about the position and the work environment with more scrutiny.

There are so many different things that go into what an in-house legal career is going to be like, and it is not the same everywhere. So, if you’re thinking of going in-house, you should evaluate the position and what it involves.

Going In-House With Microsoft

Before getting the in-house position at Microsoft, Y was working for a big law firm in Boston. Soon after, she received a job offer from Microsoft. But, the position was on the opposite end of the country, in Seattle, Washington.

Y’s new husband had recently completed his Ph.D. and just started a new job, so Y had to make the move on her own until he would be able to join her. Upon starting her job, she also found out that she was pregnant. And, if that wasn’t enough, immigration law was disrupted by the travel bans imposed by former President Trump. 

Being newly pregnant very early in her new job, she felt that she needed to outwork herself to prove her worth as a new hire. Even after her husband joined her in Seattle, she still felt that she needed to work harder.

After giving birth to her son, her husband became the stay-at-home parent and she continued to work at Microsoft for another two years. However, her hectic work schedule made her feel that she was neglecting her family.

The Turning Point

Eventually, the moment came for Y, where she questioned her path and where it was leading her. While working for Microsoft was great, and she felt appreciated by the company, her career progression was very slow. Three years in the same position was making Y feel stagnant.

Another LinkedIn recruiter came to Y with a job offer for a start-up company in business immigration called Legalpad. They needed someone who had business immigration experience to train the paralegals on how to prepare these types of O-1 alien extraordinary ability cases that Y had done at the beginning of her career and to help with sales and marketing.

She was hired on as a corporate counsel for Legalpad, where she would still get to do business immigration, but the company was helping her make the move to be a general counsel. She loved this experience and is still with Legalpad to this day.

Working At Legalpad

Legalpad strives to simplify the US immigration process. Their mission is to make the process as straightforward as possible. Currently, Legalpad focuses on start-ups and getting their founders on American soil.

Working at a start-up was very refreshing for Y. Working on a start-up does not have the structure of working for a large firm or working for a large corporation, where if you’re working for those places, you come, and they give you a job description and they tell you exactly what you need to do for your role.

In her first week, she created a chart for the CEO to determine what her role was in the company. After some restructuring, she moved to a hybrid role. In this role, she worked with compliance, ramping up to become a general counsel and immigration-specific work. After a while, she was also managing the entire legal department.

Making The Move To A Non-Legal Career

On the Former Lawyer Podcast, there is a common theme with being a lawyer, especially for immigrants and children of immigrants. There is a lot of pressure involved in your success. Becoming a lawyer had been so ingrained in Y that when she started to realize that she didn’t want to be a general counsel, after all, it was hard on her. It took Y a very long time to finally leave the law, and she fought herself every step of the way.

She moved to her non-legal career when she was promoted to Vice President of Client Services. Today, she manages the entire department, but she doesn’t do the paperwork and advising that she once did. Now, she’s focused more on the business side of running Legalpad, trying to automate and streamline the business immigration process.

Y’s Advice To Those Looking to Make the Move To A Non-Legal Career

During the interview, Y shared some great advice to people thinking about leaving their legal careers. Don’t be afraid to take that leap. It is a common feeling for lawyers to feel that their legal career is tied to their identity. Many lawyers stay in misery because they don’t know what else they can do when leaving. It might just be the best thing you can do for yourself and your family.  

If you’re interested in moving to a non-legal career, taking business classes is a really good investment. You don’t have to go out and get an MBA, but taking business classes will help you to move forward into many different types of non-legal careers. Also, evaluate your skills and strengths in comparison to different options is one of the best ways to find a new path that you’re suited for.

As always, Former Lawyer is here for you to help you make the leap from your legal career. If you haven’t yet, I invite you to download my free guide: First Steps To Leaving the Law, to help you get started with that. And, if you’re interested in legal tech, you can reach out to Y through the Legalpad website or her LinkedIn.

Get In Touch With Nhu-Y Le:

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Free Guide: First Steps To Leaving The Law:

Sarah Cottrell: Hi, and welcome to The Former Lawyer Podcast. I'm your host, Sarah Cottrell. On this show, I interview former lawyers to hear their inspiring stories about how they left law behind to find careers and lives that they love. Let's get right to the show.

Hello everyone. This week on the podcast, I am sharing my conversation with Y Le. One of the things I love about Y's story is that she shares how she incrementally moved to a point where she ended up where she is now in legal tech doing a non-legal role. I think her story and what it illustrates about how you can make small moves, and over time end up in a place that really works for you, is really helpful. I'm excited for you to hear it. Let's get right into my conversation with Y.

Hey, Y. Welcome to The Former Lawyer Podcast.

Nhu-Y Le: Thank you for having me.

Sarah Cottrell: I am really excited to hear your story. I have heard a little bit because you shared on one of the panels inside the Collaborative. But for people who haven't heard from you yet, can you introduce yourself to the listeners?

Nhu-Y Le: Hi everyone. My name is Y. I'm currently the Vice President of Client Services at Legalpad. I used to be a lawyer but I don't practice anymore and I'm really excited to share my experience and journey with everyone.

Sarah Cottrell: Yay, I'm so excited. We'll touch a little bit on a conversation around legal tech, which is of course, the arena that you are in and also some op stuff. One of the things we've been talking about in the podcast lately is how there is some overlap and there's so much new development in those areas for people who are interested in those spheres. But before we get to that, I want to start where we start on basically every episode, which is tell me why you decided to go to law school.

Nhu-Y Le: I think I always knew I wanted to be a lawyer. I grew up in Vietnam. I think even as a little kid, I was just like, “Oh, I want to be a lawyer.” When we immigrated to the US when I was eight—there are no lawyers in my family, I don't know why I had stuck in my head that I really wanted to be a lawyer—but we came to the US, I didn't speak English and still I was like, “I'm going to be a lawyer when I grow up.”

Sarah Cottrell: That's so interesting because so many people who I interview talk about deciding at a really young age that they wanted to be a lawyer. For some people, it's like, “Well, someone told me I was good at arguing and I should be a lawyer” or “I watched a lot of Law & Order,” but there also are people who have the story that you have, which is that you know you decided at an early age but you don't necessarily have a one specific thing that you can pin down that's like, “That's what set me on that path.” For you, was it that you decided at an early age like, “This is what I want to do,” and then you just progressed from there through school and to law school?

Nhu-Y Le: Yes. I'm like one of those dogs with a bone in his mouth that just won't let go. That's my personality type. I'm very stubborn and goal oriented. I was like, “I'm going to be a lawyer. No matter what, I'm going to be a lawyer.” I remember even during elementary school when we first moved to the US, I barely spoke English and I was like, “You know what, I'm going to try out to be a class representative,” and I got on the student council. This little Vietnamese girl barely spoke any English.

Sarah Cottrell: I love that.

Nhu-Y Le: Yeah. The same thing during high school, I was just like, “Yes, I'm going to be the president of the debate team. That's going to help me get into law school.” Then I took Latin in high school, no one speaks Latin, I don't know why, I just thought it would help me be a lawyer if I took that.

Sarah Cottrell: There are a lot of Latin words. I'm sure it'll come in handy. That's so awesome.

Nhu-Y Le: I don't know who taught me that because I was just like, “You can Google everything. You don't have to take that class.”

Sarah Cottrell: This comes up a lot in my conversations with people who I interview. In terms of your family, were they like, “Sure, you can do that or you can do something else,” or were they like, “Oh, yes, this is a good choice and you should go do this thing,” or was the dynamic there for you?

Nhu-Y Le: My parents were super supportive. I don't have any role models of lawyers in my family. I'm the first person in my family to be a lawyer, but my parents are just like, “Oh, you're really good at writing, you're really good at reading, you've already set your mind that this is what you want to do with your life. We don't know how to get you there but we'll support you.”

Sarah Cottrell: That's awesome. Tell me, when you got to law school, were you like, “Yes, this is everything I ever dreamed of. I'm on the path that I have planned on,” or did you have a different reaction?

Nhu-Y Le: Oh my gosh. I had such a different reaction in the sense that I still knew I wanted to be a lawyer, that was always the end goal, because again I’m very goal-oriented, but the law school process itself, as soon as I entered law school, I was like, “Wow, what a waste of time.” I did not enjoy that environment. I did not enjoy reading case laws from 200 years ago. It was not the type of experience that I thought would train me to be a lawyer. I did really well in undergrad, but to be honest, I was not a good law student because I did not thrive in that environment.

Sarah Cottrell: Honestly, there are a lot of people who have shared similar experiences on this podcast. I think it's so interesting because, and I don't know if this is your experience, but often people who didn't enjoy law school will say, “Well I didn't like it but I assumed that being a lawyer would be very different.” It is true that practicing law is in fact very different from being a law student. For you, were you telling yourself like, “I just need to get through this?” I guess you said that you still knew that you wanted to be a lawyer, but how did you tackle this experience of, “Oh, this is really not what I expected and I don't love it”?

Nhu-Y Le: Law school was the first time in my life where I questioned myself, not that I wanted to be a lawyer but questioned my abilities. Because there are things that I'm very bad at, like sports. Some things that I thankfully I'm just naturally pretty good at, academics was one of those things, I was a very good student and law school was the first time that I was like, “Wow, did I just get a C? What is happening in my life right now?” It was the first time that I really doubted my own intellectual abilities. But that aside, the law school experience, I did not enjoy the experience because I felt law school was way too long. I needed more hands-on experience but I didn't doubt that I wanted to be a lawyer during that journey.

Sarah Cottrell: Yes, I totally agree with both of those things, law school is too long and there should be more hands-on experience. Although for me at the time, I think I was just like, “Oh, research and writing.” Let's talk a little bit about, so you still knew that you wanted to be a lawyer, by the time you got to the end of law school, did you have an idea of what type of law you wanted to practice, or where were you at that point?

Nhu-Y Le: Yes, because it just thankfully landed on my lap. I went to Boston College Law School and during the second year, they had what's called Semester-in-Practice where they would place you to work at either a non-profit or a law firm and you still pay law school tuition to work there full time for all semester to get course credit. I really wanted to do that because my 1L grades were not stellar. I was probably in the bottom 30% of my class and I didn't get any slots for summer with OCI, so I was just like, “How do I get experience because I'm not going down the traditional summer associates track with my grades?” It landed in my lap because then I was placed at Fragomen, which is the top business immigration law firm in the world. When I told my parents about that though, they were very confused because they're like, “Wait, so you're paying the law school full tuition to work for a law firm for free?” I was like, “Yeah, but I have to do this because my grades are not where they need to be for me to get the experience I need.”

I ended up doing that for a whole semester in law school for course credit and afterwards, I ended up staying with Fragomen part-time for the rest of law school throughout graduation. When I graduated, I had one and a half years of experience in business immigration and it was set up for me to continue working in that field.

Sarah Cottrell: At that point, were you like, “I actively like this particular type of work,” or was it more like, “I'm in law school, I'm going to be a lawyer and this is a path to a job which is something that every law grad needs”? Where were you in terms of how you felt about the work?

Nhu-Y Le: I loved the work. I enjoyed it a lot because I'm an immigrant myself. Working for a firm that helps high-talent people come to the US was just the perfect position for me. I knew that with my personality type, working on family-based or deportation type of immigration was just too emotional for me to handle, so working for business immigration meant that I never had to go to court, I got to work with lots of very high-skilled clients. It was a quick turnaround because some cases in other spaces could drag on for years, but for business immigration, it's relatively a fast process. You know within weeks or months whether or not someone can get in or not. I loved everything about business immigration. I thought it was the perfect fit with my own immigrant experience and the types of things I like to do, which is much transactional work.

Sarah Cottrell: That's really interesting because often, I have people reach out to me and they're more traditional either on the corporate side, doing business transactions, or litigation. They'll say, “I really don't like this. I don't know that I really want to practice.” But then often, one of the practice areas that they'll mention that they're curious as to whether they would enjoy it is immigration. I think part of it is, like you said, more of the asylum type cases, which I worked on. I also worked on some pro bono asylum cases when I was practicing, which were amazing, but like you, I don't know how people do it full time because it is so emotionally taxing. I also think that sometimes, there's some opacity around what exactly exists in immigration beyond those specific types of cases. Can you just talk a little bit, for anyone who's interested in that piece of things, in terms of what the type of work that you were doing, was everyone at your firm doing that type of work or were there different types of practice within that immigration specialty? Tell me more about that.

Nhu-Y Le: Fragomen is interesting because Fragomen is considered a very large law firm but the entire firm only does business immigration. They didn't have different departments doing employment and litigation, or anything else. Everyone did business immigration. But for me when I was there, the opportunity landed on my lap to essentially lead a small team for a very large client to deal with what's called their O-1s and EB-1, which means they're aliens of extraordinary ability. These are the researchers who are creating drone research and have published patents, or the executives for that company to help those “aliens of extraordinary ability”, those top, top, top people get into the US. I really, really enjoyed it because it was much more creative. You get to really craft that whole argument as to why this person is at the top of their field in whatever it is they want to do. It was a chance to still use my writing abilities and help train paralegals to make those types of arguments for these clients.

I really enjoyed it because immigration, the way you submit things to the government, is not the same thing as legal writing which I hated. I did not enjoy Bluebook. I could care less where the comma is or if there are two spaces. To me, it's just so irrelevant. Why does this matter? But the thing with immigration writing is you actually are just writing almost a story to be like, “Hey, this person is an alien of extraordinary ability. They meet the requirement for the law based on these criteria and this is why.” You tell their story. It was a good combination between creative writing, plus fitting into the box of what the criteria were.

Sarah Cottrell: That is really interesting. You did that work for the last year and a half of law school, then you graduated, and you were working there full-time. Can you talk to me a little bit about that process, the timeline of how long you were there, because of course as you said at the beginning, you are now in a role where it's not a practicing role so I'd love to know a little bit about the progression that led you there.

Nhu-Y Le: When I graduated, after a year and a half there—and again I really enjoyed my co-workers in the team—hiring is based on need of the law firm of course so at that time, they're like, “Y, we really you but we don't have a position available for you.” That was devastating. I had all my eggs in this one basket. But the good thing is the managing partner of that law firm, he's great. I actually still talk to him from time to time. He was like, “Y, I know of this other boutique law firm that does the same thing outside D.C. I know the managing partner there. Let me make a phone call to see if they're hiring.”

They made a phone call and I found out that they were hiring. They wanted to interview me. This is when I was a 3L, I had no money and I had to get from Boston down to D.C. and I didn't have any money to get a last minute flight, I did not have a car, and the interview was the next day and I didn't have money for a hotel room. I ended up getting a train from Boston to D.C, but an overnight train so that I could sleep in the train that night, I didn't have to pay for a hotel. I got to D.C. in the morning and I changed into a suit in one of the big train stations and I got to the interview.

Sarah Cottrell: That's amazing. Tell me more about what happened with that.

Nhu-Y Le: I got the job. I guess people were just very impressed that I was so committed, I would just sleep on the train and change in the train station to work there. I was there for about nine months and it was my first time. I was waiting to see if I passed the bar and then after I passed the bar, I worked there for a few more months, then Fragomen contacted me again and said, “Hey, there's a position available back with Fragomen. Do you want to come back?” Of course, I jumped on that and I moved back to Boston and I was at Fragomen for about two and a half years doing that O-1 and EB-1 work for that high profile client. I really, really enjoyed that experience but the more I did it, the more I realized it was not sustainable on lifestyle. No matter how much you love your job, you don't want to be doing your job for 15 hours every day. I felt I wasn't taking care of my body, my relationship. I just was not in a good place near the end.

Sarah Cottrell: Yeah. Some lawyers have this perception of, “Oh, well, deals, you work a lot because of this, and trial, you work a lot because you have all of these externally imposed deadlines.” Sometimes, there can be this perception that other practice areas might not be as demanding, which in general I have not found to be accurate based on the many people that I have talked to, but can you talk a little bit about what was driving that type of work schedule for you?

Nhu-Y Le: Yeah. The client I was working with was a very, very big client and they were growing exponentially. Also, for business immigration, it's H-1B, which is a type of a visa, you can start filing it in April. That's when there's a lottery, lots of people file, you have to get it all in April. The months leading up to April, starting as early as November to April, you're working tons of hours to make sure that your cases can get filed in April. We're talking about thousands of cases. During those peak periods, it was very common for me to work 9:00 AM and then I'll stay there until 10:00 PM and just eat dinner at the firm, then take an Uber home, paid by the firm, be at the house, wake up at 5:00 AM, check my email from 5:00 AM to 8:30 AM, go back to the office at 9:00 AM and repeat.

After a while, it was not sustainable for me. Now that I have time away from it, I can fully see that now I felt like I wasn't the best version of me that I wanted to be because I was just overworked and when you get overworked, you get tired, you get grumpy, you get grouchy. I don't think I was the version of the type of friend I want it to be or the partner I want it to be or the colleague I want it to be or the manager I want it to be. Now that I have some distance from it and I went back and apologized to everyone impacted, but when you're an environment where you're just so physically and mentally tired, and apparently it comes and bring you another case for you, instead of being your happy normal self and says, “Oh, hi, how are you? Thank you,” you're like, “What do you need?” I'm ashamed to say that but that's what I did because I was not in a good space physically or mentally.

Sarah Cottrell: Yeah. I think there are many, many, many lawyers who can relate to having that experience. Tell me this, you had had this idea like, “I want to be a lawyer,” from a really young age, and so then you get to this point where you're at this firm and you're working tons of hours and you're realizing like, “This is not sustainable.” What was your reaction at the time? The reason I asked that is because often, people who become lawyers, they've been pursuing it for a long time and there's this almost panic when they realize that it isn't working. I'd love to know a little bit about how you responded when you realized, “Oh, this is not sustainable. I can't keep doing this.”

Nhu-Y Le: It's so funny because I'm a very stubborn person. I still didn't think it was, “Oh, I don't want to be a lawyer anymore,” it's like, “Oh, maybe Biglaw is not sustainable.” I was just like, “I still want to be a lawyer but maybe it's the environment that's creating this version of myself that I do not like.” I want to comment that I actually really enjoyed working there and that opportunity but it was just not who I wanted to be because of how I was reacting to the pressure of it. I was just like, “You know what, maybe I don't want to be at a Biglaw firm anymore. Maybe it's time for a change.” Around that time, through the magic of LinkedIn, a LinkedIn recruiter reached out to me and said, “Hey, do you want to go in-house?” I was like, “Maybe that's what I need instead of working at the law firm. If I go in-house, I'll get to be the client, and maybe that will be different so I can still practice but in a supposedly better work-life environment where hopefully, I can be a better version of myself.”

Sarah Cottrell: Tell me, did that happen?

Nhu-Y Le: No, it did not.

Sarah Cottrell: Tell me more.

Nhu-Y Le: My advice to everyone is that if you're thinking about “I still want to be a lawyer. Maybe I just need a change in environment,” spend some time to figure out the environment you want. I hear a lot from—and myself included—it was just like, “Well, in-house is better, in-house has to be better. In-house is going to be so cushy, nine-to-five,” but I didn't realize at that time that there are different versions of in-house, similar to different versions of the law firm. Maybe if you're at a smaller company, it's different versus a mid-size, versus a non-profit, versus a giant corporation. I ended up going in-house to Microsoft which was such an incredible opportunity. It was a team of very, very knowledgeable lawyers, but the way Microsoft in-house work, because the company is so large, the legal department was essentially a law firm that there's a thousand people in the legal department. I wish that I had taken the time to understand what different versions of in-house meant before I made that leap.

Sarah Cottrell: I think that is so important. It comes up all the time on the podcast that there's this idea that in-house might be the solution to every lawyer's problems. Sometimes, it can be. But one of the things, when people ask me for advice around going in-house, the number one thing I tell them is there is no such thing as in-house just being a monolith where you just know what the job is going to be like just because it's an “in-house” job. You really need to know what type of company it is, how big is the legal team, where are the operations of the company? Is it just domestic or is it domestic and international? So many different things go into what an in-house legal job is going to be like.

Anecdotally, in my program for lawyers who are wanting to leave, a good percentage of people who are in that program are people who went in-house in a similar experience that you had where it was like, “Okay, the firm is not working for me. I think I'm going to go in-house. Maybe that'll fix my problems,” and then they got in-house and they were like, “Oh, actually, it's this type of work and the way this work happens, that's really the problem.” Tell me, you're at Microsoft, you're in essentially a large law firm within a very large corporation and you're realizing like, “Oh, this isn't actually giving me what I was looking for,” what did you do next?

Nhu-Y Le: Let me backtrack a little bit to let you know how Microsoft started. I was living in Boston, working for a big firm in Boston at that point and then I received a job offer from Microsoft, which is on the other side of the country, it's in Washington State in Seattle. At that point in my life, I was still very, very—and I guess to a degree I still am—very career-oriented. I really wanted to just achieve my career dreams. I was recently married. My husband just completed his PhD and he just got a job working for the feds in Boston so he couldn't leave yet. We made a decision for me to basically have a long-distance marriage for me to move to Washington State by myself to work for Microsoft until he could join me at an indefinite time. Thinking back, would I have made that decision? No. It's up for everybody but I think there are things that, for me at least, I will no longer just balance career above all else. I moved to Washington State and started working for Microsoft and life happened. Two weeks after starting the job, I found out I was pregnant.

Sarah Cottrell: Oh my goodness.

Nhu-Y Le: My husband was still in Boston because he had to wrap things up and it took him about seven months to be able to move. I was pregnant with a new job on the other side of the country. This was also the time when Trump and all the travel bans came out because this was 2016. I remember starting this job, just finding out I was pregnant with all of Trump's travel bans, and I had a really difficult pregnancy. I was sick all the time, I was throwing up three times a day. I preface all of that because maybe my experience in house was different than other people who might have had a better starting point. For me, it was just the move, alone, all the Trump travel bans, which shook up the whole immigration world, and finding out I was pregnant all at the same time made the transition extremely difficult.

Sarah Cottrell: I can only imagine. With both of my girls, I had hyperemesis gravidarum, which for anyone who doesn't know what that is, it basically just means that you barf all the time, for months and months and months way past the first trimester. For me, in both cases, it was into the third trimester. Let me just tell you, a really bad situation seems even worse when you're barfing all the time. I very much sympathize with that experience. But it sounds like even if you were to take those things out, because like you said, you had these expectations of what in-house would be that wasn't necessarily accurate, so after seven months, your husband is able to move out there, what happened after that?

Nhu-Y Le: Life was still hectic, work was still hectic . I'm actually writing a book chapter right now just with other female lawyers about their definition of success. This is what the book chapter is on about this period of time in my life because I think a lot of other female lawyers, hopefully, can resonate with it, who are mothers. When I found out I was pregnant starting a new job, I felt like I had to hyper achieve because it wasn't just a new employee anymore, it was like, “Wow, I'm pregnant now I just started, I have to really show them that they did not make a bad hire.” I really felt I had to outwork myself and really, really prove to the company, myself, and my manager that I was Microsoft material. My manager, the company wasn't saying that to me but I think it was internal and it was more social and structural that I felt that I needed to do that.

During the pregnancy, it was a very difficult time where honestly, sometimes I just wouldn't eat lunch—and you can't do that when you're pregnant and throwing up three times a day—because I felt like I had to work a lot to show that I still have it, I’m meant to be here. Even after my husband moved, I still felt like I had to hyper perform to prove my worth, and again, I want to preface that it's not Microsoft said I should do that, it's not my manager had to say I had to do that, it was partially internal and partially I think maybe social. I think other mom attorneys I've spoken to have felt something similar. It's unsaid but you feel it.

Sarah Cottrell: Oh, yeah. Honestly, I think any lawyer who's listening who has experienced being pregnant as a lawyer, I'm sure would relate, because like you said, some of it is internal and then some of it is unspoken things that you're trying to overcome. Tell me what happened next.

Nhu-Y Le: I was at Microsoft for about three and a half years. It was a good experience for me because I was still a fully practicing attorney helping Microsoft employees get US work authorization and partnering with our outside counsel. That part was cool in the sense that I was the client and I got to tell outside counsel what was happening, but it was still very, very high volume. I was still working some days very, very late into the night and early morning. After I gave birth to my son, my husband actually ended up being a stay-at-home dad for two years, so that was really nice to have him home but still I felt like I didn't have time for my family because I was working a lot all the time.

The good thing about going in-house was it was the first time in my career where I actually gained skills outside of being a business immigration lawyer, where I actually got to speak with HR and other business groups and start doing M&A because for any time the company had to do any mergers and acquisition, there's always some immigration component to it. If they're trying to acquire a small startup but that startup has people that are visa dependent, they would need to loop me in to help with that part of the M&A. That was the first time in my career where I started thinking about what's outside business immigration law, the business side of things, the process side of things, how do we make the process internally more efficient, how do we collaborate with HR, recruiters, and other people.

I thought at that time, because of the scale of the company, I doubted myself. I didn't know if I was good at that part or not. It was very comforting to be like “I am a business immigration lawyer. I can do business immigration. I can review your cases, provide guidance to you.” I would do all these other projects but I'm not really sure if I'm good at this. When you're working for a large corporation, it's really easy to, because so many people are owning it, to just let someone else own it.

Sarah Cottrell: Yeah, that makes sense. You said you were there for three and a half years, what ultimately brought you to the point that you decided that you wanted to leave and what did you do next?

Nhu-Y Le: I think the moment for me was “Where am I going in my career?” I have all but good things to say about Microsoft as a company, the benefits were amazing and I really felt like the company took care of me and my family. But it's also a very large legal department in the sense that career progression is very, very slow. After three and a half years, I was still doing the exact same role and I felt like I wasn't growing in my job. I was like, “Maybe there's something more, maybe there's something different, maybe there are skills that I can be learning to really advance because my resume hasn't really changed at all during the time at Microsoft.”

Sarah Cottrell: Tell me, what did you do next in terms of how did you figure out what you wanted to do next? Because a lot of people, a lot of lawyers have this experience of like, “Okay, I don't want to be doing what I'm doing. I feel stagnant,” or “I just don't like it,” or “It's not allowing this other things in my life that I want to be able to be spending more time on,” and then they get stuck because they don't know where to go next, what to do next, many times because they went straight through from undergrad, they had planned to be a lawyer for so long that they just aren't really sure where to go next, what to do, or even what they like. Can you talk a little bit about that part of your process?

Nhu-Y Le: Yeah. This is where the magic of LinkedIn kicked in again. Honestly, my last two jobs, it just happened. The Microsoft job, the recruiter blindly reached out via LinkedIn asking if I was interested. The same thing, at this stage, after three and a half years, I was just like, “I feel like I'm not advancing my career. I'm not really gaining new skills.” I was 30, 31 at that time so I was still very, very young. I was just like, “Is this what I want to do indefinitely?” I was leaning towards, “No.” I'm still so young that I felt if I received the Microsoft job in my 40s, I would be like, “This is great. I will just work here until I retire.” But because I was 30, I was 27 when I started, maybe I didn't appreciate it as much because it's just like, “Maybe there's still more things out in the world for me to conquer.”

The magic of LinkedIn, randomly I get a LinkedIn message from a recruiter saying, “Hey, we're looking to hire for a startup, do you want to work for a startup?” I was like, “Tell me more.” The thing with the startup is that roles are extremely flexible so when I was hired, I was hired on as still in a legal role to essentially be corporate counsel. They needed someone who had business immigration experience to train the paralegals on how to prepare these types of O-1 alien extraordinary ability cases that I used to do in the beginning of my career and also to help with sales and marketing, to make sure that whatever the company was doing was compliant, in technology as well because they were building out the app.

I loved that experience because I was just like, “Well, maybe this is the perfect role for me.” I'll still get to do business immigration and they're ramping me up to hopefully be general counsel one day so that I can expand outside business immigration at a pace that's comfortable for me and the company.

Sarah Cottrell: Can you talk about the name of the company and what they do and then we'll circle back to where you went after that first role?

Nhu-Y Le: Yeah. The name of the company, and I'm still there now, it's called Legalpad. What Legalpad does is we want to simplify the US immigration process. We want to make it as easy, as simple as possible for people to come here, for foreign talent to come to the US. Right now, we focus mainly on startup founders. We help other startups get their founders into the US to start their companies.

Sarah Cottrell: That's so interesting. As someone who's only touched a little bit of the immigration system with my pro bono asylum work, I can say that anything that would simplify any part of the immigration process would be a big win. You mentioned that you started in this expressly legal role but that's not what you're doing now so can you talk to me about how that progression happened?

Nhu-Y Le: Yeah. Working on a startup does not have the structure of working for a large firm or working for a large corporation, where if you're working for those places, you come and they give you a job description and they tell you exactly what you need to do for your role. Working at a startup was very refreshing because essentially when I started, within my first week, I wrote a short chart for the CEO that says, “Hey, I think this is what my role is. I think these are the things that I should be doing in this role.” I did that for about a few months and then we had some restructuring within the company and then I moved on more to a hybrid role where I was still doing compliance work for the company, trying to ramp up because I really still thought I wanted to be general counsel one day, but then still providing insight to all the teams about training for the paralegals on how to do business immigration cases. It's a hybrid role of compliance stuff, ramping up to be corporate to general counsel but still immigration specific work, and then adding on people management because then I ended up taking over the team to be more management of the entire legal department. I don't do that job anymore. I've transitioned again.

Sarah Cottrell: Okay, tell me about that and you said at the time, you still thought you were wanting to go for the GC position which suggests to me that at some point, you had this realization that maybe that wasn't what you wanted, is that correct?

Nhu-Y Le: Correct. I was still on this track to grooming myself to be GC one day because I was still like, “Yeah, I'm a lawyer. I've only been practicing for about seven and a half, eight years, I'm not ready to stop being a lawyer yet.” When you grow up as an immigrant kid, good luck telling your parents that you don't want to be a lawyer anymore after eight years of practice.

Sarah Cottrell: Yeah. Actually, a couple months ago I interviewed Nnamdi Nwaezeapu, he wrote a book, his parents are first generation immigrants, and it's called Doctor Lawyer Engineer: How to Pursue Your Dreams without Giving Your Parents a Heart Attack. We have talked quite a bit on the podcast about that experience of being an immigrant or the child of immigrants and becoming a lawyer and some of the pressures that are involved there.

Nhu-Y Le: It was so ingrained within my identity for myself because as a child, I was like, “Y equals lawyer.” That's what I want to be. I'm going to do that. That's my mission in life and to then realize about five months ago that man, I don't want to be GC. I wanted to take a step back from being viewed as the legal person. I want to move more into process. That was a huge, huge mental shift for me. It was not overnight because I fought it every step of the way. I really, really thought I was just like, “No, maybe I should be a lawyer. I know how to do this.” It took a very long time for me to admit to myself that, “No, Y, you had your fun. You really don't want to be considered as the legal person anymore.”

Sarah Cottrell: Yeah. It's a huge shift. That's one of the things in the Collaborative that really people end up having to work on the most because you do get to this place where you're like, “This is who I am.” If I'm not a lawyer, then there's almost this existential crisis of “Who am I?” You mentioned you're more interested in the process side of things and when I hear that, I think operations and that sort of thing, is that right?

Nhu-Y Le: Yeah. What I do now is I was promoted and now my role is Vice President of Client Services. What I do is I manage the entire legal function but not as a lawyer. There are four lawyers who report to me and underneath them, there are 12 immigration specialists. I manage the entire department but I'm not the person that's signing the forms, providing direct legal advice anymore. I'm moving away from that because my job is to make sure process improvement, numbers like costs, start thinking more about the business side of how to run a profitable business. I actually, knock on wood, I applied for an online MBA so I'll know in a month if I get into the program because I realized that gosh, law school does not train you how to run a business.

Sarah Cottrell: No, it does not.

Nhu-Y Le: I want to take an MBA now because that's where I want to head. I want to be an operations person. I want to learn more about how the pieces work together so that the machine can run efficiently and have the lawyers deal with the legal stuff but not me.

Sarah Cottrell: Yeah. We've talked about legal tech and the ways in which legal tech is exploding several times in the podcast. Can you just talk briefly about the intersection between your startup, the legal tech space, the type of role you're doing, legal operations and all that stuff?

Nhu-Y Le: Yeah. Immigration is a very data-entry type of law. There are lots of forms you have to submit to the government, lots of paper that you have to submit. This is prime space to use technology to help optimize that entire process of how do we get someone who's currently outside the US into the US as quickly as possible. Law firms are quoting this person 10 weeks to prepare this petition. How can we do it shorter with less churn from both our team? Because what I tell my team is, my favorite quote right now is, “Guys, cut the fat.” What I mean by that is how do you submit a petition using technology and process improvement to streamline the process, cut out all the legal jargon, cut out all the unnecessary beautiful language that's not needed. How do you make this to the point where the petition has all the things you need to get it approvable but standardized enough that we can start automating this stuff? We don't need lawyers to write beautiful paragraphs and quote the law. To me honestly, that's not separable, but it's not necessary.

Sarah Cottrell: Some lawyers are listening and they're like, “No.”

Nhu-Y Le: I know. I will limit that to be in the immigration space, business immigration specifically, it's not necessary. There's a way to still get an approvable case by cutting all that out to automate as much as possible, so that when someone's giving you the client, has a a platform where they give you the information, it's automatically populated into all the documents and the letters you need so that you can just print out this petition for them to submit. That's the goal.

Sarah Cottrell: Right. It makes things more accessible, which of course, is always an issue when we're talking about legal services. Is there anything else that you would like to share from your story or your experience as we're getting to the end of our conversation?

Nhu-Y Le: Yeah. I think of two things. One, don't be afraid to take the leap. It's scary because I feel as lawyers, our identity becomes so tied to the fact that we're lawyers, i.e the lawyer, that it's very scary to cut that bond but it's okay. Really think about it because it might be the best decision that you've ever made for yourself and for your family. Actually, there are three things. I lied. The second thing is if anyone's interested in legal tech, reach out to me, I would love to speak to you about it. This is such an incredible space right now that has so much growth potential. I feel like every field in the law has the ability to optimize whatever it is you're doing using technology. There are lots of startups now doing contracts—we do immigration—there are lots of people trying to use technology to optimize how the field of laws practice. If you're interested in that, let me know.

The third piece of advice and guidance I have is if you're interested in moving outside of the legal field, take business classes. Maybe not a formal MBA but some business type classes. It's going to really, really help you because that's the area that I strongly feel like I need a lot of ramp up in order to move from lawyer to more of a non-lawyer business role. Because when I'm in meetings with people and they're talking about the revenue streams or costs and our burn rate, I don't speak that language well yet and I don't want to be one step behind with conversations with our finance team or our sales team because I don't understand how the business side of a company operates. I feel like that would add so much value. If you're interested in jumping out of legal to do business, take those classes. It's going to help you communicate and get buy-in from people.

Sarah Cottrell: Yeah. You know what I think is really interesting and helpful about your story, because often people who are lawyers and are like, “I want to do something else,” they gravitate towards the idea of like, “Oh, maybe if I go get another type of degree, then that will open other doors.” The thing that I think is helpful about your story is that you got into a role and then you saw where you wanted to upskill and then you're able to identify what it is that you want to learn about. It's like, “Okay, I'm going to go get the information that I need to bring back to this role that I'm already doing that I have now identified that I know that I like,” which I think for a lot of lawyers, there's sometimes this idea of like, “Well, I have a vague sense that maybe I might want to do something else so maybe I should go get some other degree and then figure out from there what it is that I really want to do.” I think your story really illustrates how getting clear on what it is that you're wanting to do next is really helpful before you go and identify it, for example, another degree like an MBA.

Nhu-Y Le: Yeah. Don't spend $100,000 on an MBA if you don't need it. Maybe what you need is honestly, a data boot camp like MR coding experience. Figuring out what you need, don't just get a vague degree for the sake of adding to your CV. It's not going to help you make the transition. Figuring out exactly what role you're trying to get and what the skills are required for that role, because I just don't have the mind for it but honestly, I feel like lawyers, if you have just basic computer programming experience, it's going to help you so much to go to even a law firm or another company and be like, “I can help you automate,” even something basic like you see all those problems you're having on Excel and how you're tracking information, “Let me build you a really quick model on how to get the data you need really quickly.”

Sarah Cottrell: Yes. My husband was a computer programmer before law school. He can do magical things in Excel that my brain does not fully comprehend. Great. If people are interested in connecting with you, learning more about you, or learning more about Legalpad, where can they find you online?

Nhu-Y Le: Yeah. To learn more about Legalpad, we have our website, it's You can check out our cool website there. To find me online, LinkedIn is really the best way to reach me. You can just look for my name on LinkedIn and I'm happy to connect with you there and add you as a connection.

Sarah Cottrell: Yes, definitely. Plug into the magic of LinkedIn. I think that's one of the things that we've learned from this conversation.

Nhu-Y Le: If you need a job, LinkedIn is where it’s at.

Sarah Cottrell: That's amazing. Thank you so much for sharing your story, Y. I really appreciate you coming on today and just being so open and letting us know all about your story.

Nhu-Y Le: Thank you for having me, Sarah. I really enjoyed speaking with you.

Sarah Cottrell: Thanks so much for listening. I absolutely love getting to share this podcast with you. If you haven't yet, I invite you to download my free guide: First Steps to Leaving the Law at Until next time, have a great week.